Jervine
Chemical compound
From Wikipedia, the free encyclopedia
Jervine is a steroidal alkaloid with molecular formula C27H39NO3 which is derived from the plant genus Veratrum. Similar to cyclopamine, which also occurs in the genus Veratrum, it is a teratogen implicated in birth defects when consumed by animals during a certain period of their gestation.[citation needed]
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| Names | |
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| IUPAC name
3β-Hydroxy-17β,23β-epoxyveratraman-11-one | |
| Systematic IUPAC name
(2â²R,3S,3â²R,3â²aS,6â²S,6aS,6bS,7â²aR,11aS,11bR)-3-Hydroxy-3â²,6â²,10,11b-tetramethyl-2,3,3â²a,4,4â²,5â²,6,6â²,6a,6b,7,7â²,7â²a,8,11a,11b-hexadecahydro-3â²H-spiro[benzo[a]fluorene-9,2â²-furo[3,2-b]pyridin]-11(1H)-one | |
| Other names
(3β,23β)-17,23-Epoxy-3-hydroxyveratraman-11-one | |
| Identifiers | |
3D model (JSmol) |
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| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.006.745 |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C27H39NO3 | |
| Molar mass | 425.60 g/mol |
| Solubility | 10 mg/mL in EtOH 6 mg/mL in DMF |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Physiological effects
Jervine is a potent teratogen causing birth defects in vertebrates. In severe cases it can cause cyclopia and holoprosencephaly.[citation needed]
Mechanism of action
Jervine's biological activity is mediated via its interaction with the 7 pass trans membrane protein smoothened. Jervine binds with and inhibits smoothened, which is an integral part of the hedgehog signaling pathways.[1] With smoothened inhibited, the GLI1 transcription cannot be activated and hedgehog target genes cannot be transcribed.[citation needed]